ES2539939T3 - Production procedures of 1,2,3,3,3-pentafluoropropene - Google Patents
Production procedures of 1,2,3,3,3-pentafluoropropene Download PDFInfo
- Publication number
- ES2539939T3 ES2539939T3 ES07796389.0T ES07796389T ES2539939T3 ES 2539939 T3 ES2539939 T3 ES 2539939T3 ES 07796389 T ES07796389 T ES 07796389T ES 2539939 T3 ES2539939 T3 ES 2539939T3
- Authority
- ES
- Spain
- Prior art keywords
- pentafluoropropene
- production procedures
- alumina
- reaction
- reacting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 abstract 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Un procedimiento para preparar 1,2,3,3,3-pentafluoropropeno, que comprende: hacer reaccionar CF3CClFCCl2F con H2 en una zona de reacción en presencia de un catalizador que comprende una cantidad catalíticamente efectiva de paladio soportado sobre un soporte seleccionado del grupo que consiste en alúmina, alúmina fluorada, fluoruro de aluminio y sus mezclas, para producir una mezcla de productos que comprende 1,2,3,3,3-pentafluoropropeno, en el que la relación en moles de H2 a CF3CClFCCl2F alimentados a la zona de reacción está entre 1:1 y 5:1.A process for preparing 1,2,3,3,3-pentafluoropropene, comprising: reacting CF3CClFCCl2F with H2 in a reaction zone in the presence of a catalyst comprising a catalytically effective amount of supported palladium on a support selected from the group that It consists of alumina, fluorinated alumina, aluminum fluoride and mixtures thereof, to produce a mixture of products comprising 1,2,3,3,3-pentafluoropropene, in which the mole ratio of H2 to CF3CClFCCl2F fed to the area of reaction is between 1: 1 and 5: 1.
Description
Tabla 1 Table 1
- T ºC T ºC
- Relación molar H2/215bb/HF 1234yf 1243zf 263fb Z-1225ye E-1225ye 245eb Z- o E-1215yb E- o Z-1215yb 226ea 215bb Molar ratio H2 / 215bb / HF 1234yf 1243zf 263fb Z-1225ye E-1225ye 245eb Z- or E-1215yb E- or Z-1215yb 226ea 215bb
- 225225
- 2/1/4 2,6 ND 1,6 16,7 18,0 29,3 5,6 4,3 ND 13,2 2/1/4 2.6 ND 1.6 16.7 18.0 29.3 5.6 4.3 ND 13.2
- 250250
- 2/1/4 3,2 ND 1,8 21,4 20,9 20,5 8,5 6,6 ND 9,3 2/1/4 3.2 ND 1.8 21.4 20.9 20.5 8.5 6.6 ND 9.3
- 275275
- 2/1/4 3,1 2,5 2,1 44,6 10,5 14,8 5,9 4,5 ND 2,7 2/1/4 3.1 2.5 2.1 44.6 10.5 14.8 5.9 4,5 ND 2.7
- 300300
- 2/1/4 3,1 2,8 1,9 43,8 10,7 2,5 10,4 4,7 ND 2,3 2/1/4 3.1 2.8 1.9 43.8 10.7 2.5 10.4 4.7 ND 2.3
- 300300
- 4/1/8 16,3 0,1 7,9 28,8 7,3 24,7 ND ND ND ND 4/1/8 16.3 0.1 7.9 28.8 7.3 24.7 ND ND ND ND
- 300300
- 1/1/8 0,7 1,2 ND 16,0 4,4 ND 19,0 9,1 9,3 33,7 1/1/8 0.7 1.2 ND 16.0 4.4 ND 19.0 9.1 9.3 33.7
- 350350
- 1/1/8 0,7 1,2 ND 9,6 1,4 ND 13,8 6,1 21,3 29,4 1/1/8 0.7 1.2 ND 9.6 1.4 ND 13.8 6.1 21.3 29.4
- 350350
- 2/1/8 3,6 1,4 ND 28,5 8,8 ND 15,3 7,1 17,0 3,8 2/1/8 3.6 1.4 ND 28.5 8.8 ND 15.3 7.1 17.0 3.8
- ND = no detectado ND = not detected
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US81664906P | 2006-06-27 | 2006-06-27 | |
US816649P | 2006-06-27 | ||
PCT/US2007/014646 WO2008002501A2 (en) | 2006-06-27 | 2007-06-22 | 1,2,3,3,3-pentafluoropropene production processes |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2539939T3 true ES2539939T3 (en) | 2015-07-07 |
Family
ID=38657962
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES07796389.0T Active ES2539939T3 (en) | 2006-06-27 | 2007-06-22 | Production procedures of 1,2,3,3,3-pentafluoropropene |
Country Status (6)
Country | Link |
---|---|
US (7) | US8263816B2 (en) |
EP (1) | EP2043980B1 (en) |
JP (1) | JP5393454B2 (en) |
CN (2) | CN101479218B (en) |
ES (1) | ES2539939T3 (en) |
WO (1) | WO2008002501A2 (en) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8766020B2 (en) | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
FI3336073T3 (en) * | 2006-01-03 | 2023-01-31 | Method for producing fluorinated organic compounds | |
CN101479218B (en) | 2006-06-27 | 2013-08-21 | 纳幕尔杜邦公司 | 1,2,3,3,3-pentafluoropropene production processes |
EP2046704A2 (en) | 2006-06-27 | 2009-04-15 | E.I. Du Pont De Nemours And Company | Tetrafluoropropene production processes |
US8377327B2 (en) | 2006-06-27 | 2013-02-19 | E I Du Pont De Nemours And Company | Tetrafluoropropene production processes |
JP5393453B2 (en) | 2006-06-27 | 2014-01-22 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Method for producing tetrafluoropropene |
EP4328213A3 (en) * | 2006-10-27 | 2024-04-03 | Honeywell International Inc. | A high purity 2,3,3,3-tetrafluoropropene |
TW200831446A (en) * | 2006-11-15 | 2008-08-01 | Du Pont | Processes for producing pentafluoropropenes and certain azeotropes comprising HF and certain halopropenes of the formula C3HCIF4 |
GB0808836D0 (en) | 2008-05-15 | 2008-06-18 | Ineos Fluor Ltd | Process |
US8487145B2 (en) | 2009-06-03 | 2013-07-16 | E I De Pont De Nemours And Company | Catalysts and process to manufacture 2,3,3,3-tetrafluoropropene |
US7985884B2 (en) | 2009-06-03 | 2011-07-26 | E. I. Du Pont De Nemours And Company | Process to manufacture 2,3,3,3-tetrafluoropropene |
US9003797B2 (en) | 2011-11-02 | 2015-04-14 | E L Du Pont De Nemours And Company | Use of compositions comprising 1,1,1,2,3-pentafluoropropane and optionally Z-1,1,1,4,4,4-hexafluoro-2-butene in power cycles |
US20130104573A1 (en) | 2011-11-02 | 2013-05-02 | E I Du Pont De Nemours And Company | Use of compositions comprising 1,1,1,2,3-pentafluoropropane and optionally z-1,1,1,4,4,4-hexafluoro-2-butene in chillers |
US20130104575A1 (en) | 2011-11-02 | 2013-05-02 | E I Du Pont De Nemours And Company | Use of compositions comprising 1,1,1,2,3-pentafluoropropane and optionally z-1,1,1,4,4,4-hexafluoro-2-butene in high temperature heat pumps |
WO2013096426A1 (en) | 2011-12-21 | 2013-06-27 | E. I. Du Pont De Nemours And Company | Use of e-1,1,1,4,4,5,5,5-octafluoro-2-pentene and optionally 1,1,1,2,3-pentafluoropropane in chillers |
EP2794804A1 (en) | 2011-12-21 | 2014-10-29 | E. I. Du Pont de Nemours and Company | Use of e-1,1,1,4,4,5,5,5-octafluoro-2-pentene and optionally 1,1,1,2,3-pentafluoropropane in high temperature heat pumps |
EP2995668A1 (en) | 2011-12-21 | 2016-03-16 | E. I. du Pont de Nemours and Company | Use of compositions comprising e-1,1,1,4,4,5,5,5-octafluoro-2-pentene in power cycles |
EP4212500A1 (en) | 2018-06-06 | 2023-07-19 | Honeywell International Inc. | Method for dehydrochlorination of hcfc-244bb to manufacture hfo-1234yf |
JP7287965B2 (en) | 2019-11-13 | 2023-06-06 | フジアン ヨンジン テクノロジー カンパニー リミテッド | A new synthetic method for 2,3,3,3-tetrafluoropropene (1234yf) and 2,3-dichloro-1,1,1-trifluoropropane (243db) |
Family Cites Families (44)
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US2437993A (en) | 1946-07-12 | 1948-03-16 | Du Pont | Fluorination of acyclic olefinic compounds |
US2466189A (en) | 1946-07-12 | 1949-04-05 | Du Pont | Process for adding fluorine to acyclic olefinic compounds |
GB938070A (en) * | 1961-04-05 | 1963-09-25 | Allied Chem | New fluorination process |
US4873381A (en) | 1988-05-20 | 1989-10-10 | E. I. Du Pont De Nemours And Company | Hydrodehalogenation of CF3 CHClF in the presence of supported Pd |
US5136113A (en) | 1991-07-23 | 1992-08-04 | E. I. Du Pont De Nemours And Company | Catalytic hydrogenolysis |
EP0726243A1 (en) * | 1992-06-05 | 1996-08-14 | Daikin Industries, Limited | Method for manufacturing 1,1,1,2,3-pentafluoropropene and method for manufacturing 1,1,1,2,3-pentafluoropropane |
JPH0687771A (en) | 1992-09-04 | 1994-03-29 | Daikin Ind Ltd | Production of 1,1,1,2,3-pentafluoropropane |
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US5326914A (en) * | 1993-05-27 | 1994-07-05 | E. I. Du Pont De Nemours And Company | Homogeneous catalytic hydrodechlorination of chlorocarbons |
DE4343169A1 (en) | 1993-12-17 | 1995-06-22 | Solvay Deutschland | Catalytic hydrodehalogenation of halogen-containing compounds from elements of the fourth main group |
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FR2729136A1 (en) | 1995-01-05 | 1996-07-12 | Atochem Elf Sa | Dehydrofluorination of fluoroalkane into fluoro:alkene |
US6369284B1 (en) * | 1997-01-31 | 2002-04-09 | E. I. Du Pont De Nemours And Company | Catalytic manufacture of pentafluoropropenes |
US6031141A (en) | 1997-08-25 | 2000-02-29 | E. I. Du Pont De Nemours And Company | Fluoroolefin manufacturing process |
FR2768717B1 (en) * | 1997-09-24 | 1999-11-12 | Solvay | PROCESS FOR SEPARATING HYDROGEN FLUORIDE FROM ITS MIXTURES WITH A HYDROFLUOROALCANE CONTAINING FROM 3 TO 6 CARBON ATOMS |
WO1999062849A1 (en) * | 1998-06-02 | 1999-12-09 | E.I. Du Pont De Nemours And Company | Process for the production of hexafluoropropylene from cc1f2cc1fcf3 and azeotropes of cc1f2cc1fcf3 with hf |
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WO2004018095A1 (en) * | 2002-08-22 | 2004-03-04 | E.I. Du Pont De Nemours And Company | Nickel-substituted and mixed nickel-and-cobalt-substituted chromium oxide compositions, their preparation, and their use as catalysts and catalyst precursors |
EP1539347B1 (en) * | 2002-08-22 | 2012-06-27 | E.I. Du Pont De Nemours And Company | Cobalt substituted chromium oxide compositions, their preparation and their use as catalysts and catalyst precursors |
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WO2005037742A1 (en) * | 2003-10-14 | 2005-04-28 | E.I. Dupont De Nemours And Company | Process for the preparation of 1,1,1,3,3,3-hexafluoropropane and at least one of 1,1,1,2,3,3-hexafluoropropane and 1,1,1,2,3,3,3-heptafluoropropane |
CA2539936C (en) * | 2003-10-14 | 2012-10-02 | E.I. Du Pont De Nemours And Company | Process for the preparation of 1,1,1,3,3-pentafluoropropane and 1,1,1,2,3-pentafluoropropane |
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EP2046704A2 (en) | 2006-06-27 | 2009-04-15 | E.I. Du Pont De Nemours And Company | Tetrafluoropropene production processes |
JP5393453B2 (en) | 2006-06-27 | 2014-01-22 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Method for producing tetrafluoropropene |
KR101394583B1 (en) | 2006-10-03 | 2014-05-12 | 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. | Dehydrogenationhalogenation process for the production of C3-C6(hydro)fluoroalkenes |
TW200838835A (en) * | 2006-11-15 | 2008-10-01 | Du Pont | Processes for producing pentafluoropropenes and azeotropes comprising HF and certain halopropenes of the formula C3CI2F4, C3CIF5, or C3HF5 |
FR2948362B1 (en) * | 2009-07-23 | 2012-03-23 | Arkema France | PROCESS FOR THE PREPARATION OF FLUORINATED COMPOUNDS |
BR112021022059A2 (en) * | 2018-10-26 | 2021-12-28 | Chemours Co Fc Llc | Fluoropropene compositions, methods of producing a mixture and cooling, processes for transferring heat, for treating a surface and for forming a composition, refrigeration system, refrigeration apparatus, use of the fluoropropene composition and method for replacing a soda |
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2007
- 2007-06-22 CN CN2007800237034A patent/CN101479218B/en active Active
- 2007-06-22 WO PCT/US2007/014646 patent/WO2008002501A2/en active Application Filing
- 2007-06-22 US US12/301,065 patent/US8263816B2/en active Active
- 2007-06-22 JP JP2009518190A patent/JP5393454B2/en active Active
- 2007-06-22 EP EP20070796389 patent/EP2043980B1/en active Active
- 2007-06-22 CN CN201310308829.3A patent/CN103396288B/en active Active
- 2007-06-22 ES ES07796389.0T patent/ES2539939T3/en active Active
-
2012
- 2012-07-02 US US13/539,963 patent/US20120267567A1/en not_active Abandoned
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2013
- 2013-10-10 US US14/050,636 patent/US10392545B2/en active Active
-
2019
- 2019-07-01 US US16/458,350 patent/US11053421B2/en active Active
-
2021
- 2021-06-02 US US17/336,575 patent/US11708516B2/en active Active
-
2023
- 2023-06-06 US US18/206,127 patent/US11912923B2/en active Active
- 2023-11-10 US US18/506,244 patent/US20240076536A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
CN103396288B (en) | 2016-12-28 |
WO2008002501A3 (en) | 2008-03-20 |
CN103396288A (en) | 2013-11-20 |
US11912923B2 (en) | 2024-02-27 |
EP2043980A2 (en) | 2009-04-08 |
WO2008002501A2 (en) | 2008-01-03 |
JP5393454B2 (en) | 2014-01-22 |
EP2043980B1 (en) | 2015-04-29 |
US11708516B2 (en) | 2023-07-25 |
CN101479218A (en) | 2009-07-08 |
JP2009542652A (en) | 2009-12-03 |
CN101479218B (en) | 2013-08-21 |
US11053421B2 (en) | 2021-07-06 |
US20210292627A1 (en) | 2021-09-23 |
US20240076536A1 (en) | 2024-03-07 |
US20190322917A1 (en) | 2019-10-24 |
US20230313012A1 (en) | 2023-10-05 |
US20090264690A1 (en) | 2009-10-22 |
US10392545B2 (en) | 2019-08-27 |
US20120267567A1 (en) | 2012-10-25 |
US20140034870A1 (en) | 2014-02-06 |
US8263816B2 (en) | 2012-09-11 |
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